THE BEHAVIOUR OF p-QUINONES TOWARDS WITTIG-HORNER REAGENTS

Abstract

Triethylphosphonoacetate (I) reacts with p-quinones (1, 2) to give the corresponding 4-hydroxyl-β-hydroxy-succinic acid diethyl acetate 4 and 5, respectively. On the other hand, the reaction of Wittig-Horner reagent (I) with p-chloranil (3) afforded 2,3,5,6-tetrachloro-4-hydroxyphenyl-β-hydroxy-succinic acid diethyl acetate (7) and the diethyl phosphonate adduct (6). Possible reaction mechanisms are considered and the structural assignments are based on compatible analytical and spectroscopic results.

Key Words:

• triethylphosphonoacetate (I)
• p-quinones 1-3
• 4-hydroxy-phenyl-β-hydroxy-succinic acid diethylacetate (4)
• 4-hydroxynaphthyl-β-hydroxysuccinic acid diethyl acetate (5)
• 2,3,5,6-tetrachloro-4-hydroxyphenyl-β-hydroxy-succinic acid diethyl acetate (7
• and the diethylphosphonate adduct (6)